Patent GB-613040-A (GB)
Title: Improvements in and relating to the preparation and use of substituted methane compounds
IPC: C07C303/32
Filed: 1945-10-30
Abstract: Salts of tri- and tetra-substituted methane (T.S.M.) compounds are manufactured by condensing a benzene, naphthalene or anthracene mono- or poly-sulphonic acid, which may carry hydroxy or halogen substituents provided at least one replaceable hydrogen atom remains in the ring, with an aldehyde (other than formaldehyde or carbohydrates) or a substance yielding it, or a ketone, amide or imide, and then converting the resulting T.S.M. compound into a salt of copper, silver, gold, calcium, barium, zinc, aluminium, lead, arsenic, bismuth, chromium, mercury, manganese, iron or nickel, or of an organic base; or by condensing the aldehyde, ketone, amide or imide with a preformed salt of the parent sulphonic acid or with the free sulphonic acid in the presence of the salt-forming component (i.e. a hydroxide, oxide or salt of one of the specified metals or an organic base or a salt thereof).  The organic bases may be primary, secondary or tertiary amines, preferably carrying an active group such as that of an arsonic acid or a phosphorus acid, or organic compounds having other active groups such as cetyltrimethylammonium or other bacteriostatic basic radicals, or especially antiseptic substances of the acridine or sulphanilamide series, specified bases (or salts thereof) being cetyltrimethylammonium bromide, 4-bromosulphanilamide, ethyl p-aminobenzoate, sulphanilamide, methyl m-amino-p-hydroxybenzoate and guanidine carbonate.  The reaction is generally carried out in solution, preferably in water, but where necessary in a non-aqueous solvent, e.g. ethyl alcohol, and may be effected by heating, with or without agitation, if desired in the presence of a condensing agent of dehydrating type, e.g. sulphuric acid or phosphorus oxychloride. The products, which have bactericidal and fungicidal properties which make them useful for treating burns, wounds and other lesions, or as rotproofing and mould preventing agents for the preservation of protein, cellulosic materials or timber, are soluble in a solution of an excess of the corresponding T.S.M. compounds or of the parent sulphonic acids or of different T.S.M. compounds or of di-substituted methane compounds, and solutions may in some cases be obtained directly by using the reaction components in other than stoichiometric proportions. Examples describe the preparation of salts of T.S.M. compounds obtained from, on the one hand, naphthalene-2-sulphonic acid, 2-naphthol-6-sulphonic acid or anthracene-b -sulphonic acid, and, on the other hand, acetaldehyde, benzaldehyde, anisaldehyde, vanillin, piperonal, acetone, octyl aldehyde, benzophenone or urea. Specifications 547,564 and 552,751 are referred to.ALSO:Salts of tri- and tetra-substituted methane (T.S.M.) compounds are manufactured by condensing a benzene, naphthalene or anthracene mono- or polysulphonic acid, which may carry hydroxy or halogen substituents provided at least one replaceable hydrogen atom remains in the ring, with an aldehyde (other than formaldehyde or carbohydrates) or a substance yielding it, or a ketone, amide or imide, and then converting the resulting T.S.M. compound into a salt of an organic base, or by condensing the aldehyde, ketone, amide or imide with a performed salt of the parent sulphonic acid or with the free sulphonic acid in the presence of the organic base or a salt thereof. The organic bases may be antiseptic substances of the acridine series.  The reaction is generally carried out in solution, preferably in water, but where necessary, in a non-aqueous solvent, e.g. ethyl alcohol, and may be effected by heating, with or without agitation, if desired in the presence of a condensing agent of dehydrating type, e.g. sulphuric acid or phosphorus oxychloride. The products, which have bactericidal and fungicidal properties which make them useful for treating burns, wounds and other lesions, or as rot-proofing and mould preventing agents for the preservation of protein, cellulosic materials or timber, are soluble in a solution of an excess of the corresponding T.S.M. compounds or of the parent sulphonic acids or of different T.S.M. compounds or of di-substituted methane compounds and solutions may in some cases be obtained directly by using the reaction components in other than stoichiometric proportions.  Examples describe the preparation of salts of T.S.M. compounds obtained from, on the one hand, naphthalene-2-sulphonic acid, 2-naphthol-6-sulphonic acid or anthracene-b -sulphonic acid, and, on the other hand, acetaldehyde, benzaldehyde, anisaldehyde, vanillin, piperonal, acetone, octyl aldehyde, benzophenone or urea.  Specifications 547,564 and 552,751 are referred to.